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Showing papers on "Wieland–Miescher ketone published in 2010"


Journal ArticleDOI
TL;DR: Ureas, carbamoyl derivatives, amides, and sulfonamides can be easily prepared from the strained (R,R)-cylohexanediamine urea in high yield, leaving a free amino group that shows good catalytic activity in intramolecular aldol condensations.
Abstract: Ureas, carbamoyl derivatives, amides, and sulfonamides can be easily prepared from the strained (R,R)-cylohexanediamine urea (1) in high yield, leaving a free amino group that shows good catalytic activity in intramolecular aldol condensations. The preparation of Wieland−Miescher ketone has been studied with these catalysts.

34 citations



Journal ArticleDOI
TL;DR: In this paper, a 4-h biotransformation of Hajos-Parrish ketone using the strain of Didymosphaeria igniaria was described.
Abstract: Enantiospecific microbial reduction of bicyclic ketones was described. Racemic Wieland–Miescher (1) and Hajos–Parrish (2) ketones were used as substrates. In a 4-h biotransformation of Hajos–Parrish ketone (2) using the strain of Didymosphaeria igniaria an optically pure ketone (R)-2 was obtained, whereas the (S)-2 ketone underwent reduction to (4aS,5S)-4 alcohol with 100% of enantiomeric excess and with over 60% of diastereoisomeric excess. Jones oxidation of the alcohol obtained in the biotransformation gave an optically pure ketone (S)-2. Enzymatic system of Coryneum betulinum reduced the (R)-2 ketone to (4aR,5S)-4 alcohol with a high enantiomerical purity in a 6-day reaction. Wieland-Miescher (1) ketone was transformed by these microorganisms in an analogous way, but the reaction times were longer.

6 citations


Journal ArticleDOI
TL;DR: In this article, the authors presented a study that was supported by the Ministerio de Ciencia e Innovació (Spain)-FEDER through projects CTQ2007-67661338/BQU, CTQ 2007-62771 /BQU and Consolider Ingenio 2010 CSD2007-00006.
Abstract: This research was supported by the Ministerio de Ciencia e Innovacion (Spain)-FEDER through projects CTQ2007- 61338/BQU, CTQ2007-62771/BQU and Consolider Ingenio 2010 CSD2007-00006. Thanks are also due to the Comissionat per a Universitats i Recerca (Catalonia) for Grant 2005SGR-00442, Generalitat Valenciana for Grant (GVPRE/ 2008/006) and the University of Alicante (GRJ06-05).